The present invention relates to a process for the preparation of hydroxyalkylphenyl ether compounds. More particularly, the present invention is concerned with an improved catalyst for use in the preparation of hydroxyalkylphenyl ether compounds by the reaction of cyclic organic carbonate compounds with phenols.
Carlson disclosed in U.S. Pat. No. 2,448,767 a method of hydroxyethylation wherein ethylene carbonate or ethylene sulfite was reacted with certain organic compounds including phenols and alcohols. The reaction could be carried out in the presence or in the absence of a suitable solvent, and in the presence or in the absence of a suitable catalyst. Catalysts that were disclosed included an acid (concentrated sulfuric acid or an alkyl ester of sulfuric acid), a base (alkali carbonates), or the alkali salt of a phenol. The preferred catalyst was an alkali carbonate or alkali salt of a phenol. U.S. Pat. No. 3,283,030 disclosed the use of potassium carbonate as a basic catalyst in the reaction of ethylene carbonate with certain substituted phenols.
Alkali metal hydrides disclosed by U.S. Pat. Nos. 2,987,555 and 2,967,892 have also been found to be effective catalysts for alkoxylation reactions of ethylene carbonate with phenols and chloromethylethylene carbonate with phenols respectively.
One disadvantage associated with prior art processes using acidic or basic catalysts has been the occurrence of secondary reactions between the hydroxyalkylphenyl ether product and the carbonate reactant forming quantities of undesirable side-products. A further disadvantage of known prior art processes is the inability to use certain modified phenolic compounds that are unstable under acidic or basic reaction conditions.